NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	218.06
Volume:	218.338
LogP:	2.432
LogD:	1.875
LogS:	-3.417
# Rotatable Bonds:	1
TPSA:	63.6
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.777
Synthetic Accessibility Score:	2.428
Fsp3:	0.167
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.657
MDCK Permeability:	2.454910281812772e-05
Pgp-inhibitor:	0.005
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.304
30% Bioavailability (F30%):	0.381

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.151
Plasma Protein Binding (PPB):	94.23457336425781%
Volume Distribution (VD):	0.475
Pgp-substrate:	2.0185494422912598%

ADMET: Metabolism

CYP1A2-inhibitor:	0.98
CYP1A2-substrate:	0.834
CYP2C19-inhibitor:	0.623
CYP2C19-substrate:	0.145
CYP2C9-inhibitor:	0.62
CYP2C9-substrate:	0.614
CYP2D6-inhibitor:	0.814
CYP2D6-substrate:	0.29
CYP3A4-inhibitor:	0.706
CYP3A4-substrate:	0.178

ADMET: Excretion

Clearance (CL):	8.322
Half-life (T1/2):	0.613

ADMET: Toxicity

hERG Blockers:	0.021
Human Hepatotoxicity (H-HT):	0.6
Drug-inuced Liver Injury (DILI):	0.54
AMES Toxicity:	0.822
Rat Oral Acute Toxicity:	0.927
Maximum Recommended Daily Dose:	0.918
Skin Sensitization:	0.683
Carcinogencity:	0.843
Eye Corrosion:	0.056
Eye Irritation:	0.964
Respiratory Toxicity:	0.796

Download Data

Data Type	Select
General Info & Identifiers & Properties
Structure MOL file
Source Organisms
Biological Activities
Similar NPs/Drugs

Natural Product: NPC198305

Natural Product ID:	NPC198305
*Common Name:**	3-Methoxy-7-Methyljuglone
IUPAC Name:	8-hydroxy-2-methoxy-6-methylnaphthalene-1,4-dione
Synonyms:
Standard InCHIKey:	KDBWUCIHUALFON-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C12H10O4/c1-6-3-7-8(13)5-10(16-2)12(15)11(7)9(14)4-6/h3-5,14H,1-2H3
SMILES:	COC1=CC(=O)c2c(C1=O)c(O)cc(c2)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL449429
PubChem CID:	5276616
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000023] Naphthalenes [CHEMONTID:0000153] Naphthoquinones

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[12713396]
NPO16657	Diospyros maritima	Species	Ebenaceae	Eukaryota	bark	Indonesia	n.a.	PMID[15270571]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	roots	n.a.	n.a.	PMID[20022509]
NPO18296	Diospyros kaki	Species	Ebenaceae	Eukaryota	n.a.	calyx	n.a.	PMID[21561086]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21866899]
NPO16657	Diospyros maritima	Species	Ebenaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22313254]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23325115]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	Roots	n.a.	n.a.	PMID[23541646]
NPO18296	Diospyros kaki	Species	Ebenaceae	Eukaryota	n.a.	fruit	n.a.	PMID[24086493]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28140583]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7381508]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16657	Diospyros maritima	Species	Ebenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18296	Diospyros kaki	Species	Ebenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16657	Diospyros maritima	Species	Ebenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18296	Diospyros kaki	Species	Ebenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO16657	Diospyros maritima	Species	Ebenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO18296	Diospyros kaki	Species	Ebenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO18296	Diospyros kaki	Species	Ebenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO16657	Diospyros maritima	Species	Ebenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18296	Diospyros kaki	Species	Ebenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
ED50	4
IC50	8
Others	8

Activity Type	# Activity
Cell Line	4
Organism	16

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	ED50	=	2.4	ug ml-1	PMID[547086]
NPT1034	Cell Line	Lu1	Homo sapiens	ED50	=	1.8	ug ml-1	PMID[547086]
NPT858	Cell Line	LNCaP	Homo sapiens	ED50	=	4.1	ug ml-1	PMID[547086]
NPT737	Cell Line	HUVEC	Homo sapiens	ED50	=	5.5	ug ml-1	PMID[547086]
NPT729	Organism	Micrococcus luteus	Micrococcus luteus	IC50	=	700.0	ug.mL-1	PMID[547086]
NPT729	Organism	Micrococcus luteus	Micrococcus luteus	Activity	>	1000.0	ug ml-1	PMID[547086]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	IC50	>	1000.0	ug.mL-1	PMID[547086]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	Activity	>	1000.0	ug ml-1	PMID[547086]
NPT602	Organism	Mycobacterium smegmatis	Mycobacterium smegmatis	IC50	>	1000.0	ug.mL-1	PMID[547086]
NPT602	Organism	Mycobacterium smegmatis	Mycobacterium smegmatis	Activity	>	1000.0	ug ml-1	PMID[547086]
NPT1513	Organism	Mycobacterium avium	Mycobacterium avium	IC50	=	700.0	ug.mL-1	PMID[547086]
NPT1513	Organism	Mycobacterium avium	Mycobacterium avium	Activity	>	1000.0	ug ml-1	PMID[547086]
NPT20	Organism	Candida albicans	Candida albicans	IC50	>	1000.0	ug.mL-1	PMID[547086]
NPT85	Organism	Filobasidiella neoformans	Cryptococcus neoformans	IC50	>	1000.0	ug.mL-1	PMID[547086]
NPT85	Organism	Filobasidiella neoformans	Cryptococcus neoformans	Activity	>	1000.0	ug ml-1	PMID[547086]
NPT312	Organism	Saccharomyces cerevisiae	Saccharomyces cerevisiae	IC50	>	1000.0	ug.mL-1	PMID[547086]
NPT312	Organism	Saccharomyces cerevisiae	Saccharomyces cerevisiae	Activity	>	1000.0	ug ml-1	PMID[547086]
NPT21	Organism	Aspergillus niger	Aspergillus niger	IC50	>	1000.0	ug.mL-1	PMID[547086]
NPT21	Organism	Aspergillus niger	Aspergillus niger	Activity	>	1000.0	ug ml-1	PMID[547086]
NPT20	Organism	Candida albicans	Candida albicans	Activity	>	1000.0	ug ml-1	PMID[547086]

☑ Note for Activity Records:
☉ The quantitative biological activities were primarily integrated from ChEMBL (Version-30) database and were also directly collected from PubMed literature. PubMed PMID was provided as the reference link for each activity record.

Chemically structural similarity: I. Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes 4,3285 NPs with experimentally-derived bioactivity available in NPASS)

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules. Tc lies between [0, 1] where '1' indicates the highest similarity. What is Tanimoto coefficient

● The left chart: Distribution of similarity level between NPC198305 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	327
0.1-0.2	1563
0.2-0.3	3731
0.3-0.4	10005
0.4-0.5	9430
0.5-0.6	5906
0.6-0.7	7988
0.7-0.8	3307
0.8-0.85	325
0.85-0.9	101
0.9-0.95	10
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9683	High Similarity	NPC309430
0.9677	High Similarity	NPC237225
0.9516	High Similarity	NPC51037
0.9453	High Similarity	NPC254603
0.9355	High Similarity	NPC310540
0.9302	High Similarity	NPC171968
0.9291	High Similarity	NPC278928
0.9225	High Similarity	NPC88864
0.9213	High Similarity	NPC165257
0.9206	High Similarity	NPC231774
0.9194	High Similarity	NPC307174
0.9154	High Similarity	NPC193169
0.9098	High Similarity	NPC173980
0.9	High Similarity	NPC205360
0.8968	High Similarity	NPC135062
0.8952	High Similarity	NPC206778
0.8952	High Similarity	NPC285829
0.8923	High Similarity	NPC199253
0.8923	High Similarity	NPC27659
0.8923	High Similarity	NPC136588
0.8906	High Similarity	NPC306765
0.8906	High Similarity	NPC1991
0.8898	High Similarity	NPC68756
0.8898	High Similarity	NPC152525
0.8889	High Similarity	NPC477408
0.8846	High Similarity	NPC146647
0.8846	High Similarity	NPC34414
0.8841	High Similarity	NPC29932
0.8806	High Similarity	NPC86524
0.8788	High Similarity	NPC70622
0.8779	High Similarity	NPC55949
0.8777	High Similarity	NPC474630
0.8769	High Similarity	NPC282923
0.876	High Similarity	NPC3224
0.8759	High Similarity	NPC283292
0.8759	High Similarity	NPC110810
0.875	High Similarity	NPC142956
0.875	High Similarity	NPC114620
0.875	High Similarity	NPC103337
0.8731	High Similarity	NPC281513
0.8731	High Similarity	NPC22222
0.8722	High Similarity	NPC52407
0.8714	High Similarity	NPC136878
0.8712	High Similarity	NPC205992
0.8682	High Similarity	NPC123506
0.8682	High Similarity	NPC287473
0.8672	High Similarity	NPC375356
0.8667	High Similarity	NPC315275
0.8667	High Similarity	NPC474311
0.8657	High Similarity	NPC50924
0.8647	High Similarity	NPC477406
0.8647	High Similarity	NPC246693
0.8647	High Similarity	NPC110609
0.8647	High Similarity	NPC242358
0.8643	High Similarity	NPC28632
0.8636	High Similarity	NPC31799
0.8636	High Similarity	NPC475741
0.8629	High Similarity	NPC108288
0.8626	High Similarity	NPC48248
0.8615	High Similarity	NPC15837
0.8615	High Similarity	NPC96915
0.8605	High Similarity	NPC74507
0.8605	High Similarity	NPC234890
0.8603	High Similarity	NPC471452
0.8594	High Similarity	NPC164947
0.8594	High Similarity	NPC282577
0.8594	High Similarity	NPC300274
0.8583	High Similarity	NPC472046
0.8582	High Similarity	NPC59459
0.8582	High Similarity	NPC225051
0.8582	High Similarity	NPC53896
0.8571	High Similarity	NPC477409
0.8571	High Similarity	NPC244699
0.8571	High Similarity	NPC17083
0.8571	High Similarity	NPC232178
0.8561	High Similarity	NPC99731
0.8548	High Similarity	NPC161304
0.8538	High Similarity	NPC131799
0.8538	High Similarity	NPC103540
0.8529	High Similarity	NPC232996
0.8529	High Similarity	NPC155211
0.8527	High Similarity	NPC273683
0.8519	High Similarity	NPC288089
0.8507	High Similarity	NPC58685
0.85	High Similarity	NPC469885
0.85	High Similarity	NPC143898
0.8496	Intermediate Similarity	NPC117609
0.8496	Intermediate Similarity	NPC253488
0.8492	Intermediate Similarity	NPC41567
0.8489	Intermediate Similarity	NPC124365
0.8478	Intermediate Similarity	NPC1268
0.8478	Intermediate Similarity	NPC26924
0.8473	Intermediate Similarity	NPC227741
0.8473	Intermediate Similarity	NPC160499
0.8473	Intermediate Similarity	NPC136342
0.8473	Intermediate Similarity	NPC49647
0.8473	Intermediate Similarity	NPC295202
0.8467	Intermediate Similarity	NPC301341
0.8467	Intermediate Similarity	NPC284184
0.8467	Intermediate Similarity	NPC264022
0.8467	Intermediate Similarity	NPC305060
0.8462	Intermediate Similarity	NPC173978
0.8456	Intermediate Similarity	NPC22644
0.8456	Intermediate Similarity	NPC161632
0.8456	Intermediate Similarity	NPC283088
0.8456	Intermediate Similarity	NPC80035
0.8444	Intermediate Similarity	NPC263817
0.8444	Intermediate Similarity	NPC115458
0.8444	Intermediate Similarity	NPC314048
0.844	Intermediate Similarity	NPC471906
0.8429	Intermediate Similarity	NPC69755
0.8421	Intermediate Similarity	NPC171460
0.8417	Intermediate Similarity	NPC315578
0.8409	Intermediate Similarity	NPC45537
0.8409	Intermediate Similarity	NPC471530
0.8394	Intermediate Similarity	NPC272268
0.8394	Intermediate Similarity	NPC254847
0.8394	Intermediate Similarity	NPC141934
0.8394	Intermediate Similarity	NPC38158
0.8394	Intermediate Similarity	NPC474813
0.8394	Intermediate Similarity	NPC475549
0.8392	Intermediate Similarity	NPC476821
0.8385	Intermediate Similarity	NPC182646
0.8385	Intermediate Similarity	NPC275145
0.838	Intermediate Similarity	NPC474309
0.838	Intermediate Similarity	NPC475923
0.8359	Intermediate Similarity	NPC7151
0.8359	Intermediate Similarity	NPC216297
0.8359	Intermediate Similarity	NPC473662
0.8358	Intermediate Similarity	NPC31539
0.8346	Intermediate Similarity	NPC179898
0.8345	Intermediate Similarity	NPC143438
0.8345	Intermediate Similarity	NPC306835
0.8345	Intermediate Similarity	NPC476477
0.8345	Intermediate Similarity	NPC111422
0.8345	Intermediate Similarity	NPC256463
0.8345	Intermediate Similarity	NPC299405
0.8345	Intermediate Similarity	NPC471602
0.8345	Intermediate Similarity	NPC29771
0.8345	Intermediate Similarity	NPC190457
0.8345	Intermediate Similarity	NPC216312
0.8333	Intermediate Similarity	NPC471905
0.8333	Intermediate Similarity	NPC53414
0.8333	Intermediate Similarity	NPC477453
0.8333	Intermediate Similarity	NPC254492
0.8333	Intermediate Similarity	NPC245923
0.8333	Intermediate Similarity	NPC53206
0.8322	Intermediate Similarity	NPC300540
0.8321	Intermediate Similarity	NPC199273
0.8321	Intermediate Similarity	NPC474766
0.8321	Intermediate Similarity	NPC258502
0.831	Intermediate Similarity	NPC79627
0.8296	Intermediate Similarity	NPC85342
0.8296	Intermediate Similarity	NPC93015
0.8286	Intermediate Similarity	NPC147542
0.8286	Intermediate Similarity	NPC241349
0.8286	Intermediate Similarity	NPC37992
0.8286	Intermediate Similarity	NPC327916
0.8286	Intermediate Similarity	NPC32749
0.8286	Intermediate Similarity	NPC156872
0.8286	Intermediate Similarity	NPC183345
0.8286	Intermediate Similarity	NPC220496
0.8286	Intermediate Similarity	NPC42262
0.8276	Intermediate Similarity	NPC474310
0.8273	Intermediate Similarity	NPC416
0.8273	Intermediate Similarity	NPC61590
0.8273	Intermediate Similarity	NPC13715
0.8273	Intermediate Similarity	NPC61398
0.8273	Intermediate Similarity	NPC4214
0.8271	Intermediate Similarity	NPC72667
0.8264	Intermediate Similarity	NPC252208
0.8261	Intermediate Similarity	NPC472308
0.8254	Intermediate Similarity	NPC240163
0.8248	Intermediate Similarity	NPC202225
0.8248	Intermediate Similarity	NPC12070
0.8239	Intermediate Similarity	NPC66593
0.8235	Intermediate Similarity	NPC312560
0.8227	Intermediate Similarity	NPC305845
0.8227	Intermediate Similarity	NPC204045
0.8227	Intermediate Similarity	NPC84273
0.8227	Intermediate Similarity	NPC257003
0.8227	Intermediate Similarity	NPC471444
0.8222	Intermediate Similarity	NPC108129
0.8214	Intermediate Similarity	NPC242994
0.8214	Intermediate Similarity	NPC138099
0.8214	Intermediate Similarity	NPC295339
0.8209	Intermediate Similarity	NPC96024
0.8207	Intermediate Similarity	NPC470479
0.8207	Intermediate Similarity	NPC112816
0.8201	Intermediate Similarity	NPC475957
0.8195	Intermediate Similarity	NPC472047
0.8188	Intermediate Similarity	NPC249272
0.8182	Intermediate Similarity	NPC48762
0.8182	Intermediate Similarity	NPC274085
0.8182	Intermediate Similarity	NPC236189
0.8182	Intermediate Similarity	NPC244691
0.8182	Intermediate Similarity	NPC193703
0.8182	Intermediate Similarity	NPC89664
0.8182	Intermediate Similarity	NPC21599
0.8175	Intermediate Similarity	NPC78307

Chemically structural similarity: II. Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

● The left chart: Distribution of similarity level between NPC198305 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	308
0.1-0.2	985
0.2-0.3	1518
0.3-0.4	2739
0.4-0.5	2074
0.5-0.6	1057
0.6-0.7	405
0.7-0.8	59
0.8-0.85	3
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8629	High Similarity	NPD405	Clinical (unspecified phase)
0.8538	High Similarity	NPD1470	Approved
0.8394	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.8231	Intermediate Similarity	NPD1201	Approved
0.8014	Intermediate Similarity	NPD2346	Discontinued
0.7905	Intermediate Similarity	NPD3226	Approved
0.7746	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.774	Intermediate Similarity	NPD3300	Phase 2
0.7692	Intermediate Similarity	NPD2935	Discontinued
0.7687	Intermediate Similarity	NPD7390	Discontinued
0.7639	Intermediate Similarity	NPD1471	Phase 3
0.7569	Intermediate Similarity	NPD5404	Approved
0.7569	Intermediate Similarity	NPD5408	Approved
0.7569	Intermediate Similarity	NPD5406	Approved
0.7569	Intermediate Similarity	NPD5405	Approved
0.7517	Intermediate Similarity	NPD2532	Approved
0.7517	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7517	Intermediate Similarity	NPD2534	Approved
0.7517	Intermediate Similarity	NPD2533	Approved
0.75	Intermediate Similarity	NPD9493	Approved
0.7483	Intermediate Similarity	NPD1607	Approved
0.7466	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7465	Intermediate Similarity	NPD943	Approved
0.7464	Intermediate Similarity	NPD1164	Approved
0.7463	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7447	Intermediate Similarity	NPD2313	Discontinued
0.74	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7397	Intermediate Similarity	NPD2344	Approved
0.7379	Intermediate Similarity	NPD2799	Discontinued
0.7358	Intermediate Similarity	NPD6232	Discontinued
0.7343	Intermediate Similarity	NPD1240	Approved
0.7329	Intermediate Similarity	NPD7473	Discontinued
0.7287	Intermediate Similarity	NPD9266	Approved
0.7287	Intermediate Similarity	NPD74	Approved
0.7286	Intermediate Similarity	NPD2798	Approved
0.7279	Intermediate Similarity	NPD2932	Approved
0.7266	Intermediate Similarity	NPD1283	Approved
0.726	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.726	Intermediate Similarity	NPD1510	Phase 2
0.7209	Intermediate Similarity	NPD9263	Approved
0.7209	Intermediate Similarity	NPD9264	Approved
0.7209	Intermediate Similarity	NPD9267	Approved
0.7206	Intermediate Similarity	NPD1651	Approved
0.7203	Intermediate Similarity	NPD411	Approved
0.72	Intermediate Similarity	NPD2309	Approved
0.7188	Intermediate Similarity	NPD6959	Discontinued
0.7181	Intermediate Similarity	NPD2800	Approved
0.7172	Intermediate Similarity	NPD447	Suspended
0.7153	Intermediate Similarity	NPD3019	Approved
0.7153	Intermediate Similarity	NPD4626	Approved
0.7135	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD7819	Suspended
0.7133	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD7003	Approved
0.7122	Intermediate Similarity	NPD9717	Approved
0.7121	Intermediate Similarity	NPD1609	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD8150	Discontinued
0.7092	Intermediate Similarity	NPD1203	Approved
0.7068	Intermediate Similarity	NPD7635	Approved
0.705	Intermediate Similarity	NPD1281	Approved
0.705	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD3882	Suspended
0.704	Intermediate Similarity	NPD288	Approved
0.7029	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD1876	Approved
0.7013	Intermediate Similarity	NPD1512	Approved
0.7	Intermediate Similarity	NPD1549	Phase 2
0.7	Intermediate Similarity	NPD3972	Approved
0.7	Intermediate Similarity	NPD7075	Discontinued
0.6987	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.698	Remote Similarity	NPD1551	Phase 2
0.6977	Remote Similarity	NPD1237	Approved
0.6966	Remote Similarity	NPD3764	Approved
0.6963	Remote Similarity	NPD5951	Approved
0.6963	Remote Similarity	NPD9281	Approved
0.696	Remote Similarity	NPD844	Approved
0.6947	Remote Similarity	NPD2342	Discontinued
0.6943	Remote Similarity	NPD4380	Phase 2
0.6943	Remote Similarity	NPD6599	Discontinued
0.6933	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD5710	Approved
0.6933	Remote Similarity	NPD5711	Approved
0.6919	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6917	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6908	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6908	Remote Similarity	NPD3750	Approved
0.6899	Remote Similarity	NPD9261	Approved
0.6894	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6892	Remote Similarity	NPD6651	Approved
0.6884	Remote Similarity	NPD9545	Approved
0.6883	Remote Similarity	NPD1511	Approved
0.6879	Remote Similarity	NPD7458	Discontinued
0.6875	Remote Similarity	NPD9494	Approved
0.6875	Remote Similarity	NPD289	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD4060	Phase 1
0.6864	Remote Similarity	NPD5034	Approved
0.6864	Remote Similarity	NPD4954	Approved
0.6864	Remote Similarity	NPD5026	Approved
0.6864	Remote Similarity	NPD5028	Approved
0.6864	Remote Similarity	NPD4955	Approved
0.6864	Remote Similarity	NPD36	Approved
0.6855	Remote Similarity	NPD1934	Approved
0.6846	Remote Similarity	NPD164	Approved
0.6842	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD4750	Phase 3
0.6839	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD5691	Approved
0.6824	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD8312	Approved
0.6824	Remote Similarity	NPD230	Phase 1
0.6824	Remote Similarity	NPD8313	Approved
0.6818	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD2801	Approved
0.6805	Remote Similarity	NPD5031	Approved
0.6805	Remote Similarity	NPD5030	Phase 2
0.6805	Remote Similarity	NPD5027	Approved
0.6805	Remote Similarity	NPD5029	Approved
0.6803	Remote Similarity	NPD520	Approved
0.68	Remote Similarity	NPD4308	Phase 3
0.6797	Remote Similarity	NPD8166	Discontinued
0.6786	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD6799	Approved
0.677	Remote Similarity	NPD5402	Approved
0.677	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD1247	Approved
0.6765	Remote Similarity	NPD1241	Discontinued
0.6761	Remote Similarity	NPD9269	Phase 2
0.6761	Remote Similarity	NPD6534	Approved
0.6761	Remote Similarity	NPD6535	Approved
0.676	Remote Similarity	NPD6780	Approved
0.676	Remote Similarity	NPD6777	Approved
0.676	Remote Similarity	NPD6782	Approved
0.676	Remote Similarity	NPD6781	Approved
0.676	Remote Similarity	NPD6778	Approved
0.676	Remote Similarity	NPD6776	Approved
0.676	Remote Similarity	NPD6779	Approved
0.6757	Remote Similarity	NPD2979	Phase 3
0.6755	Remote Similarity	NPD6099	Approved
0.6755	Remote Similarity	NPD6100	Approved
0.675	Remote Similarity	NPD6801	Discontinued
0.674	Remote Similarity	NPD7435	Discontinued
0.6738	Remote Similarity	NPD3023	Approved
0.6738	Remote Similarity	NPD3026	Approved
0.6735	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6715	Remote Similarity	NPD497	Approved
0.6715	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6714	Remote Similarity	NPD3024	Approved
0.6714	Remote Similarity	NPD3025	Approved
0.6714	Remote Similarity	NPD9268	Approved
0.6713	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6713	Remote Similarity	NPD1755	Approved
0.6712	Remote Similarity	NPD6832	Phase 2
0.6705	Remote Similarity	NPD5037	Approved
0.6705	Remote Similarity	NPD5038	Approved
0.669	Remote Similarity	NPD1019	Discontinued
0.669	Remote Similarity	NPD1611	Approved
0.6689	Remote Similarity	NPD6663	Approved
0.6688	Remote Similarity	NPD4628	Phase 3
0.6687	Remote Similarity	NPD3749	Approved
0.6687	Remote Similarity	NPD7411	Suspended
0.6667	Remote Similarity	NPD845	Approved
0.6667	Remote Similarity	NPD2296	Approved
0.6667	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3817	Phase 2
0.6667	Remote Similarity	NPD3751	Discontinued
0.6648	Remote Similarity	NPD7700	Phase 2
0.6648	Remote Similarity	NPD7696	Phase 3
0.6648	Remote Similarity	NPD7699	Phase 2
0.6648	Remote Similarity	NPD7697	Approved
0.6648	Remote Similarity	NPD7698	Approved
0.6647	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD5036	Approved
0.6647	Remote Similarity	NPD6166	Phase 2
0.6646	Remote Similarity	NPD6844	Discontinued
0.6646	Remote Similarity	NPD920	Approved
0.6646	Remote Similarity	NPD919	Approved
0.6645	Remote Similarity	NPD2796	Approved
0.6644	Remote Similarity	NPD5736	Approved
0.6643	Remote Similarity	NPD4878	Approved
0.6643	Remote Similarity	NPD1608	Approved
0.6642	Remote Similarity	NPD1398	Phase 1
0.6642	Remote Similarity	NPD2182	Approved
0.6642	Remote Similarity	NPD496	Approved
0.6642	Remote Similarity	NPD495	Approved
0.6642	Remote Similarity	NPD498	Approved
0.6641	Remote Similarity	NPD1930	Approved
0.6641	Remote Similarity	NPD1929	Approved
0.6641	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6627	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6627	Remote Similarity	NPD5844	Phase 1
0.6626	Remote Similarity	NPD7768	Phase 2
0.6623	Remote Similarity	NPD1243	Approved
0.6622	Remote Similarity	NPD3268	Approved
0.6612	Remote Similarity	NPD8320	Phase 1
0.6612	Remote Similarity	NPD7871	Phase 2

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data